


Her Fantasy

by Swan_Secrets



Category: Supernatural
Genre: Anal, Anal Fingering, Anal Sex, Canon Het Relationship, Community: spnkink_meme, F/M, First Time, Het
Language: English
Status: Completed
Published: 2014-02-12
Updated: 2014-02-12
Packaged: 2018-01-12 02:15:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,488
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1180707
Author URL: https://archiveofourown.org/users/Swan_Secrets/pseuds/Swan_Secrets
Summary: <blockquote class="userstuff">
              <p>Written for a prompt at the spn_kinkmeme: "Sam and a woman (Jess? Pamela? Lisa?) having anal sex and loving it. (no pegging, Sam must be the one penetrating the other)"</p>
<p>Jess has a fantasy she shares with Sam, they fulfil it together.</p>
            </blockquote>





	Her Fantasy

"Are you sure?" 

"Yes. You can stop asking" 

"Okay." 

"If I didn't want this I wouldn't have brought it up in the first place." 

"Okay," Sam nodded. He was sitting on the bed in Jess' dorm room. Her roommate was at her boyfriend's place, giving them privacy for the remainder of the night. Jess was beside him. They were holding hands. 

"Accept that you have an awesome girlfriend who wants to try anal with you." 

Sam smiled. "I accepted I have an awesome girlfriend a long time ago." 

She kissed him on the lips but pulled back just as things were heating up. "Stay. Right there." She stood and gave his cheek a quick peck then scampered off into the bedroom. 

Sam rubbed his palms on his thighs and took a deep breath. Anal sex was something completely new for him too. When Jess had first brought up the subject he hadn't quite known how to react. He'd never given it that much thought before in all honesty. Jess had told him that it had been a little bit of a secret fantasy of hers for a while now and that she thought she was ready to trust him and share that fact with him. They had talked about it a few times, and they had decided that tonight was the night. They'd had a nice dinner and some nice wine and here they were. About to do it. About to lose their anal virginity. 

Sam had heard guys talking about anal sex plenty of times in the past. All of them had been very enthusiastic about what a great time they'd had. Sam himself had been a little curious, but beyond that hadn't taken interest. Maybe it was because in his experience vaginal sex was so fantastic. 

The bathroom door opened and for a few moments Sam Winchester was incapable of having any kind of rational thought. 

Jessica Moore looked phenomenal. She was wearing lingerie he had never seen her in before. He licked his lips. She leaned against the doorframe of the bathroom, posing. The underwear was scarlet. Lace. The bra pushed her tits up and together. There was a frilly pink strip under her bust and along the top of the waistband of her matching panties. 

"I take it by the drool you like?" 

"Uh-huh," Sam said and started to stand. 

"No. Stay there. Right there." She reached back into the bathroom then approached the bed with a tube in her right hand. She set the tube on the table beside the bed. Sam saw it was 'Xtra Glide Lube'. His eye returned to his girlfriend. He gulped. She was beyond beautiful. She was like an angel. He could feel himself starting to get hard. 

Jess stood right in front of him. He looked down her body. Her breasts. Her slim figure. Her hips. Her long legs. He wanted her. He wanted to fuck her. He looked up and met her gaze and he could see there in her eyes that she wanted to fuck him too. 

"You're going to fuck my ass tonight Sam," she said. She ran both hands over her breasts, squeezing them together. 

Sam gulped again and nodded, he was rubbing his hands on his thighs again. She put her hands on his shoulders and leaned in to whisper in his ear. 

"I've fantasised about it. About you. This morning I masturbated thinking about what we're about to do." 

"I've been thinking about it too," Sam said. And he had. He'd thought about what it would be like. What it would feel like. He'd watched porn. He'd read a few articles online 

"Tell me what you've been thinking about," her hand moved down his chest. "Tell me Sam." 

"I...uh, I was thinking about you. Naked. I was thinking about kissing you all over." 

"Mmm and then?" Jessica kept moving her hand down. 

"Putting my fingers inside you." 

"Inside where?" Jess slid her hand onto the crotch of his jeans. She smiled at the bulge she encountered. 

"In your ass." 

Jess rubbed her palm against his bulge. "Did you think about putting anything else in there?" 

"My penis." 

Jess paused. Then pulled away. "Dirty talk isn't really our thing huh?" 

There was a beat then they both burst out laughing. 

"No, guess not," Sam chuckled. 

"Good thing I've always thought actions speak louder than words," Jess purred and started unbuttoning his shirt. He reached around her, reaching for the clasp of her bra. "Leave it for now," she said. "This is going to be special. Let me make it special for you." 

"Every time is special with you," Sam replied. From anyone else that would have sounded corny, but Jess knew that Sam actually meant it, the big softy that he was. 

Once she'd unbuttoned it all the way Sam helped her take off his shirt. Next she undid his belt, then took a few steps back. "Take of your pants, leave on your shorts," she said. 

"Yes ma'am," Sam said. He stood and did as she said. It clicked in Sam that this was Jess' fantasy and that to give her the best experience he should follow her lead. She had obviously thought this all through in great detail. As big as deal as this was for him he knew it was a bigger deal for her. It was her fantasy. It was her ass that was going to be penetrated. Sam unbuttoned and in a kind of slow, and he hoped sexy, way he slid down his jeans. He stepped out of them, shorts tented by the erection beneath. 

Jess looked at him and bit her bottom lip. Sam had no idea what a gigantic cup of yummy he was. Those broad shoulders, the defined but not overly developed muscles, those soulful eyes. She knew under his shorts there was a beautiful cock that was just waiting for her. 

"I love you," Jess said. 

"I love you too," Sam replied. 

She motioned for him to sit back on the bed. He did. Jess turned away from him and took a few steps further away. The scarlet panties clung to her butt in a delicious way. Sam's cock twitched to full hardness. She swayed her hips from side to side. She knew exactly where his eyes were focused. 

Jess reached around behind her back and undid her bra. She kept wiggled her butt as she slowly slid one strap off her shoulder, then the other. She shrugged off the garment and let it fall to the floor. She shrugged off the garment and let it fall to the floor. She kept her bare back to Sam. She stayed like that, swaying, and he could tell form the movements of her arms she was playing with her boobs. Sam wanted to see. He wanted to see her breasts. He wanted to touch them. Kiss them. Suck them. But he sat. He waited. This was Jess' big night. 

She turned to him, covering her tits with her hands. She smiled at him and walked back towards him, with each step uncovering more of her breast until she was right in front of him with just her nipples covered. 

Sam leaned forward. He licked the finger covering her right nipple. She pulled it away and he repeated the lick on the nipple itself. Sam circled it with his tongue then licked over it again. He flicked the peak with the tip of his tongue then sucked it into his mouth. 

Jess let him kiss and suck on her nipples for a minute then gently pushed his forehead away from her chest. He had the urge to pull her down onto his lap, push her underwear to the side and thrust into her. 

Jess smiled at him and then turned away from him again. Sam clenched his hands into fists. he wanted her so bad. He watched her as she got a chair and set it about half a meter from the bed in front of him. The chair was wood, the seat was square and large and padded, and it had rounded arms. She took the tube of lubricant from the bedside table and put it on the seat of the chair. "Take off your shorts and sit back down. Show me your cock Sam." 

Sam stood. He slid down his shorts then sat down. His cock stood proud. Hard. Ready. 

Jess looked at him and bit her bottom lip. "I've been practising. Getting ready for tonight." 

"What have you been practising?" Sam asked. 

"Let me show you." 

Sam swallowed loudly. 

Jess faced away from him and bent over, pulling down her underwear at the same time. Sam's eye followed the progress of the underwear's journey to the floor. Without looking back at him she got on the chair, kneeling, her hands braced on its back, her knees on the seat. She writhed and thrust her hips like she was riding some invisible man sitting on the chair. 

She looked back at him. He looked ready to pounce. "Stay there, right there, don't make me cuff you." 

"Cuff me?" 

"I picked up a few other things while I was getting the lube, so you better be a good boy." 

"I'll be a good boy," Sam said. As much as he wanted to touch her there was something deeply sexy about watching his girlfriend like this. 

Jessica Moore shuffled her knees back and bent over. He got a great view of her pussy and her asshole. There it was. Her back door. Her rear entrance. Her chocolate starfish. Her anus. It was where he was going to fuck her tonight. Virgin territory. He was going to be the first person to fuck her there. 

He watched as she out her left hand between her legs. He could see she was wet. She used her index and middle fingers to rub up and down between her moist lips. 

Outside the room, in the hallway, there was the sound of a drunken yell. Neither Sam nor Jess paid any attention. The outside world didn't matter. Everything they wanted and everything wanted to think about was right her in this room. 

Jess moved her hand further back, she touched her asshole with the tip of her middle finger and slowly circled it. Sam put his right hand on his cock. He put this thumb against the head of it and rubbed side to side. 

The blonde woman picked up the lube and popped off the cap. She squeezed a dollop of it onto her hand and gave the middle finger of her left hand a thick coating. It was cool and gooey to the touch. She moved the hand down between her legs and back to her butt. She returned to her asshole. She ran her finger in circles around the darkened ring of skin. 

Sam rubbed a little harder. So did Jess. Faster. Over her butthole. She applied more lubricant, then more still. Her asshole and all around it was shiny with the gloop. 

"This is how I've been practising," she said and after reapplying the lubricant to her finger she pressed it to her asshole. She slowly, steadily, started to work her finger inside. 

Sam watched. still touching himself. 

She made a sharp hissing sound, Sam wondered if she had hurt herself. But she didn't stop. Once the tip of her finger up to the first knuckle was inside she twisted the figner then withdrew it. More lube. Then she slid her finger back in. It went deeper this time. She carefully worked it to the second knuckle, twisting. 

Jess continued sliding the finger in, until eventually it was all the way inside. "I've been doing this. Fingering myself. Thinking about your cock being here." She looked around at him. "Come here. Use your finger on me." She pulled her own finger out. Sam nodded. Jess got of the chair and moved the chair closer then got back on it. Jess handed him the tube of lube. He leaned forward. He kept his right hand on his cock, his other hand went to her ass. He squeezed her buttock, massaging. 

It was silly but he was kinda nervous. He was worried that maybe he would hurt her or wouldn't be good at pleasuring her anally. 

Sam made first contact with her asshole with his thumb while he cupped her bottom. She bent further forward and made an encouraging moan. He stroked with his thumb. His eyes were on her asshole. Her tight, pretty asshole. He thought. He hesitated. What he was thinking about wasn't something she'd mentioned at all. He decided he would do it. He leaned in closer, prepared for her to tell him to stop. 

Jess gasped in surprise when Sam's tongue touched her asshole. He swiped at it again with the flat of her tongue. "Is this..." 

"It's good," she interrupted him. "Keep going." 

Sam kept going. The lube didn't really taste of anything. He licked her asshole enthusiastically, using the same kind of light flicking strokes he would use on her clit. Judging by her moaning it was a good choice. 

"Oh fuck Sam, I never... Oh god that feels so good." 

 

  
Jessica's roommate was called Kelly. 

Kelly's current boyfriend was a guy named Brady. 

Or at least that's what she thought. 

Brady was only too happy to make sure Jess and Sam got plenty of quality time together. The plan was still a good long way off and he needed him as much as in love with her as possible. Brady had introduced Sam and Jess to each other a few months ago, and to his delight they had hit it off perfectly. 

Brady was possessed by the demon Sitri, and he had the honor of playing a significant role in getting Sam Winchester into position to play his part in Lucifer's plan. 

Kelly was also pretty hot so it wasn't exactly a chore to keep her out of the way and make sure Sam got his fuck on. 

Sitri had gotten Kelly pretty drunk, and had persuaded her to let him blindfold her and handcuff her to the headboard of his bed. 

He wished he was fucking Jess. But that was completely off the table, he couldn't risk ruining the carefully laid scheme. So he took out his frustrations on Kelly. Judging by her moaning as he pounded her furiously she didn't mind one bit. 

In his head though it was Jess he was making his bitch, not her roommate. 

 

  
Sam slowed his licking of her asshole while he applied lube to his fingers. 

With care and attention to her reactions he built up, finger her ass with one, then two fingers. He didn't take long to get over the last of his mental barriers around anal sex. While he used his right hand on her ass his left was between her legs, rubbing her clit in lazy circles, constantly moving. They took their time. They did everything slow and steady. 

Finally she turned to him again and said, "I think I'm ready." 

Sam and Jess got on the bed, her on her back with a stack of pillows under her butt and him on his knees. As he put on a condom then covered his hard cock in lubricant Jess was playing with her nipples, pinching and pulling on them. She spread her legs wide. 

Sam reached and slathered more of the lube on her rear hole as he moved in between her legs. She looked down at him, at the hard cock dangling from him, glistening with the thick coat of lube. She raised her legs and he hooked his arm under her right leg, resting it upon her shoulder as he moved on top. She took hold of his cock, guiding it between her legs and aiming below his usual target. 

"If you want to stop anytime, just say so," Sam said. 

Jess nodded. Then there was the unmistakable sound of her farting. They looked at each other. She held his gaze for a moment then burst out laughing. Sam joined her. 

"One of the dangers of playing back there," Jess said amongst the chuckles. "Okay. Okay." Jess took a few deep breaths. 

"I love you," said Sam. 

"I love you," Jess said. "Now put your dick in my ass." 

Sam shifted forward. 

This was it. It was happening. Jess looked at his face as she felt his hard organ touch her anus. She gave a low whimpering sound from the back of her throat when he pressed ahead. He stopped. She nodded. "Keep going. Keep going," she said. So Sam did. He pushed the head of his cock into the tight ring of muscle. 

He kept hold of his cock with his right hand, his left went to her breast, stroking his thumb over her nipple before pinching it. He applied just the amount of pressure he knew she liked. 

Sam continued slowly, slowly, slowly sliding into her. 

She hissed, an expression of pain flashed over her features, and he froze again. She waited a moment then nodded. "Okay. It's okay just hurt for a second there." 

Sam eased back, almost all the way out again. He pinched her nipple again and leaned in to give her lips a light kiss. Jess put her hand between her legs and started teasing her clit, starting off slow and getting faster. Sam waited another few seconds then resumer his journey, cautiously. 

Jess bit her bottom lip and let out a soft moan. He slid in deeper. Deeper. She moaned again. Deeper. It felt good. Really good. She was tight and hot around his cock. It was different than being in her pussy, physically and mentally. There was this extra little thrill that they were doing something kinky. 

He pinched her nipple. She kept working her clit. She moaned, louder this time. 

"Oh, oh Sam. That feels so good. So fucking good." 

"Feels good for me too." 

Jess closed her eyes and left herself just enjoy the new and exciting sensations. 

There was another couple of points where they came to a stop when it hurt for Jess. Sam back off a little then started again both times. Once he was all the way in he stopped moving and they started kissing. Their kisses were slow and romantic. Their tongues lightly went into each other's mouth and over each other. Their hands were constantly In motion, stroking and squeezing each other. 

Jess started moving her hips in a sedate rolling motion. Even though it wasn't much the movement felt fantastic for both of them. It caused a spark to flare between them, their kisses became increasingly heated. 

"Fuck me Sam, fuck my ass, fuck me," Jess said with an almost needy tone. 

Like everything else so far tonight they worked together, steadily finding and building up their rhythm. Sam squirted more lube onto his sheathed cock and her asshole. Jess was relaxed and she didn't think she had ever felt this turned on before. Her fantasy had become real and fortunately it had been everything she could have hoped for. She held onto Sam with her right hand she started fingering her cunt. She was very wet. She curled and twisted her fingers inside her pussy. 

They kissed. They both moaned and panted. Sam was careful not to get carried away, he knew if he lost control he could still easily hurt her. 

When Jess came her ass tightened and Sam had to stop thrusting because it became too difficult. He watched her face, beautiful as always, as she lost herself to bliss. 

As son as they could they went back at it. They returned to their fucking, grinding rhythm. It didn’t take long for Jess to peak again, and this time Sam joined her, cock pumping hot cum into the condom. 

They stayed together, kissing. Holding each other. They stayed while they caught their breath. 

Sam eventually moved away from her. He went to the bathroom and got rid of the condom in the trash can. When he returned he saw Jess wiping herself with a towel. "I need a shower," she said. 

They met halfway between the bed and the bathroom and wrapped their arms around each other. 

"Was that okay?" Sam asked. 

"It was way more than okay. It was exactly what I wanted," she replied. "Come on, let's get in the shower." 

Jess took him by the hand and led him into the bathroom. She got the water going and while they waited for it to heat she turned and kissed Sam. "Thank you. Really it was perfect." 

Sam smiled. "So what other things did you pick up while you were getting the lube, handcuffs?" 

Jess looked at him with a wicked sparkle in her eye. "You'll just have to wait and see Winchester."


End file.
